Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$11,000 - $11,000
June 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
July 2026
SuMoTuWeThFrSaWeek
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2
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$10,000
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$10,000
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$10,000
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$10,000
26
27
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30
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$11,000
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$11,000
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$11,000
23
24
25
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30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
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$10,000
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7
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$10,000
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$10,000
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21
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$10,000
27
28
29
30
 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$5,500 - $10,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
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7
8
9
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11
12
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20
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22
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$8,300
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
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$10,000
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$10,500
19
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$10,500
26
27
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29
30
31
 $11,000
August 2026
SuMoTuWeThFrSaWeek
 1
$11,000
2
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$11,000
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$11,000
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$11,000
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28
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$9,000
30
31
 $9,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
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$9,000
6
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$5,500
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$5,500
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21
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$5,500
27
28
29
30
 $5,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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DONAK

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Property Details
Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
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5
6
$6,000
7
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$6,000
14
15
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$6,000
21
22
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27
$7,000
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
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$10,000
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$10,000
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$10,000
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$10,000
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30
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
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$17,000
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$17,000
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$12,000
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$10,000
30
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 $7,000
September 2026
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$7,000
27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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ROSKH

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Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets

Experience the epitome of summer living at East Chop Oak Bluffs in this delightful waterfront retreat. Nestled amidst the serenity of the beachfront, this cozy home boasts a private dock...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
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$6,000
7
8
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$6,000
14
15
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$6,000
21
22
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$6,000
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$10,000
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$10,000
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$10,000
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$10,000
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30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
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$10,000
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$10,000
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$10,000
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24
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$10,000
30
31
 $8,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
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$8,000
6
7
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10
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$6,000
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$6,000
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21
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24
25
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$6,000
27
28
29
30
 $6,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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INGAE

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Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,000 - $9,750
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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$5,750
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$5,750
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$5,750
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$7,000
28
29
30
 $9,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$9,750
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6
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$9,750
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13
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$9,750
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21
22
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25
$9,750
26
27
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29
30
31
 $11,000
August 2026
SuMoTuWeThFrSaWeek
 1
$11,000
2
3
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5
6
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$11,000
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$11,000
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21
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$11,000
23
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$11,000
30
31
 $7,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,750
6
7
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9
10
11
12
$7,000
13
14
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19
$6,900
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21
22
23
24
25
26
$6,800
27
28
29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $9,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
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17
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19
20
$6,500
21
22
23
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25
26
27
$7,500
28
29
30
 $8,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
7
8
9
10
11
$9,000
12
13
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$9,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$12,000
9
10
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13
14
15
$12,000
16
17
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21
22
$12,000
23
24
25
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28
29
$8,500
30
31
 $6,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$5,500
13
14
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$5,500
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $8,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,300
7
8
9
10
11
12
13
$6,900
14
15
16
17
18
19
20
$7,400
21
22
23
24
25
26
27
$7,900
28
29
30
 $8,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,700
5
6
7
8
9
10
11
$8,700
12
13
14
15
16
17
18
$8,900
19
20
21
22
23
24
25
$9,200
26
27
28
29
30
31
 $9,400
August 2026
SuMoTuWeThFrSaWeek
 1
$9,400
2
3
4
5
6
7
8
$10,700
9
10
11
12
13
14
15
$11,200
16
17
18
19
20
21
22
$10,700
23
24
25
26
27
28
29
$9,500
30
31
 $8,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,200
6
7
8
9
10
11
12
$6,600
13
14
15
16
17
18
19
$5,600
20
21
22
23
24
25
26
$4,600
27
28
29
30
 $4,300
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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KNOXA

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Property Details
Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,600 - $8,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$3,600
28
29
30
 $4,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
8
9
10
11
$4,200
12
13
14
15
16
17
18
$4,200
19
20
21
22
23
24
25
$4,200
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$10,500
16
17
18
19
20
21
22
$10,500
23
24
25
26
27
28
29
$4,500
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$3,850
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
 $3,600
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POWDA

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Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $8,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,500
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$11,500
23
24
25
26
27
28
29
$9,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PRIAN

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$7,950 - $8,250
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
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22
23
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25
26
27
28
29
30
 $7,950
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,950
5
6
7
8
9
10
11
$7,950
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
 $8,250
August 2026
SuMoTuWeThFrSaWeek
 1
$8,250
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$8,250
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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LECAY

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Property Details
Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $6,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
31
 $8,000
August 2026
SuMoTuWeThFrSaWeek
 1
$8,000
2
3
4
5
6
7
8
$8,000
9
10
11
12
13
14
15
$8,000
16
17
18
19
20
21
22
$8,000
23
24
25
26
27
28
29
$4,500
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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COONC

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Property Details
The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem

Designed by a renowned island architect and custom-crafted,  The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home.  The exterior of the house maintains...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$4,400 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,400
7
8
9
10
11
12
13
$4,400
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$8,000
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$9,000
9
10
11
12
13
14
15
$9,000
16
17
18
19
20
21
22
$9,000
23
24
25
26
27
28
29
$9,000
30
31
 $8,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
 $6,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Two-week minimum stay per owner! 

 

 

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BEG21

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Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $8,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $6,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
31
 $7,000
August 2026
SuMoTuWeThFrSaWeek
 1
$7,000
2
3
4
5
6
7
8
$8,000
9
10
11
12
13
14
15
$8,000
16
17
18
19
20
21
22
$8,000
23
24
25
26
27
28
29
$8,000
30
31
 $3,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Note: Owner maintains security camera on front of house

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BURBR

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Property Details
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,950 - $7,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,950
7
8
9
10
11
12
13
$7,950
14
15
16
17
18
19
20
$7,950
21
22
23
24
25
26
27
$7,950
28
29
30
 $7,950
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,950
5
6
7
8
9
10
11
$7,950
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
 $7,950
August 2026
SuMoTuWeThFrSaWeek
 1
$7,950
2
3
4
5
6
7
8
$7,950
9
10
11
12
13
14
15
$7,950
16
17
18
19
20
21
22
$7,950
23
24
25
26
27
28
29
$7,950
30
31
 $7,950
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,950
6
7
8
9
10
11
12
$7,950
13
14
15
16
17
18
19
$7,950
20
21
22
23
24
25
26
$7,950
27
28
29
30
 $7,950
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HOD28

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Property Details
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,750 - $7,850
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,750
7
8
9
10
11
12
13
$5,750
14
15
16
17
18
19
20
$5,750
21
22
23
24
25
26
27
$7,850
28
29
30
 $8,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,100
5
6
7
8
9
10
11
$8,250
12
13
14
15
16
17
18
$8,250
19
20
21
22
23
24
25
$8,250
26
27
28
29
30
31
 $8,250
August 2026
SuMoTuWeThFrSaWeek
 1
$8,250
2
3
4
5
6
7
8
$9,000
9
10
11
12
13
14
15
$9,000
16
17
18
19
20
21
22
$9,000
23
24
25
26
27
28
29
$9,000
30
31
 $6,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,750
6
7
8
9
10
11
12
$6,750
13
14
15
16
17
18
19
$6,750
20
21
22
23
24
25
26
$6,750
27
28
29
30
 $5,750
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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